Uncharted Waters
by curiouswriter
Summary: Damon Salvatore, one of the world's most prestigious white-collar criminals is made a deal by the agent who caught him to help solve a case in exchange for his freedom. While Damon learns that trust might not be such a bad thing after all, Agent Gilbert discovers that things aren't always as black and white as they seem as she begins to bend the rules for the man she loves. AU/AH.
1. Chapter 1

_**AN:** Hey guys! This is the new story I was on about and I'm super excited to post this. I've been planning it for a while, laying down the foundations of the story and basically trying to make it the best that it can be. I have so many ideas where this story is going to go and I just hope that you guys will be along for the ride with me!_

_Before I start this, I would just like to say a big thank-you to my beta, cdaye8184 for making sure that the chapter was up to scratch so that I could post it!_

_This story is inspired by the television shows White Collar & The Vampire Diaries._

* * *

**Uncharted Waters**

Chapter One

_"Look at him, Look at me,  
__That boy is bad,  
__And honestly,  
__He's a wolf in disguise,  
__But I can't stop staring in those evil eyes,"_

_Monster - Lady Gaga_

* * *

Elena groaned and buried her head further into the pillow as the alarm clock on her bedside table rung off next to her for the third time. She knocked the alarm clock off the table, effectively silencing the annoying screeching and rolled over onto her back, grateful for the peaceful silence that filtered the room. It wasn't like she didn't like getting up for work in the mornings, in fact she loved waking up for work. What she didn't love was being woken up by an alarm clock that sounded more like a ticking time bomb. It wasn't the most soothing of sounds considering she'd encountered her fair share of bombs in the past. Looking down to the broken clock on her floor, she quickly moved to the bedside table and picked up her phone, checking the time.

She almost let out another groan as she took in the time flashing on her phone. Well wasn't that just was wonderful. She had about an hour and half to shower, get dressed and make it halfway across Manhattan if she wanted to make it into the office on time. Of course she'd find a way to make it happen though, she would just have to make some sacrifices to her morning routine, which would most likely be her morning coffee... again.

Elena inwardly groaned at the fact that she would be drinking the stale coffee back at the office and not her recently bought fresh cocoa beans from France. Funny enough, she'd not even had the chance to try them because for one reason or another she never had the time to have a decent cup of coffee for what seemed like forever, in fact this was the first time she had woken up in her own bed and not the comfortable office chairs for almost a week; all thanks to Damon Salvatore.

Damon Salvatore was the bane of her life. Debatably, the most renowned White Collar criminal to ever not be caught, he was cocky, arrogant and was on the top of Elena's very own personal F.B.I's most wanted list. As well as being confirmed as the man who forged Raphael's 'The Deposition of Christ', which had an estimated value of over ten million dollars, he was also suspected of committing many other crimes ranging from theft, breaking and entering to forging other priceless antiques and paintings, while also being involved in some of the most famous bank robberies and art gallery thefts in the world.

Elena's mind wandered to the Raphael painting. He'd even had the nerve to sign it, almost as if he was sending out a personal invitation to me, one saying "Come catch me, if you can". The small 'DS' insignia was blended into the colors with the faintest black so that you could barely see his initials and it took our top analysts weeks to catch the tiny, insignificant difference from the forgery that he made to the exquisite original. However, she had a gut feeling that the small game of spot the difference was just a test that he'd given the F.B.I, to see if they were a challenge or threat towards him.

She was given his case two years ago when the agent who handled the case before her, Agent Matthews retired at the healthy age of seventy two. To this day, she still remembered the small portion of advice he'd given her before walking out the door on her first day.

"Good luck catching him. The man is a ghost."

Those were Agent Matthew's famous last words that had stuck with her through the years. He wasn't lying when he said them either. In the two years that she'd been chasing Damon as her main case for the bureau, the closest that she had ever been to him was merely knowing that he was in the same city as her. The man was a chess player and planned five moves ahead of everyone else, making it almost impossible to catch him. She had to learn that the hard way a long time ago.

After showering and getting dressed into a pair of smart black trousers, white linen shirt and a black blazer, Elena was ready for another day of "pointlessly trying to catch thin air" as one of her best friends, Caroline, put it. She wasn't wrong though, that's what it seemed like with Damon.

Maybe if she was lucky, she'd be given another small case on the side. A priceless painting robbery or something, anything to just get her mind off Damon Salvatore. Elena enjoyed taking on the small cases. They were like the word-searches that you would find on the back of a newspaper or inside a magazine to her. Nothing too hard, just something to get her mind going. To give her brain a small rest from thinking about him.

Elena quickly checked the watch on her wrist, as she bounced into her kitchen. She had forty-five minutes to get to work and if she cut through Fifth Avenue, She would probably make it there in thirty minutes if she left now. Before rushing out of the apartment, she quickly picked up an apple from her fruit bowl for the journey before her eyes landed on the small document, resting on the surface of her kitchen counter.

_**'PETITION FOR DISSOLUTION OF MARRIAGE' **_  
_** 'BETWEEN ELENA MARIE DONOVAN & MATTHEW GRAHAM DONOVAN'**_

Her fingers glided over the sheet of paper. In hindsight, you'd think that if anything were to count as a distraction, it would be the divorce of her husband. But the cruel reality was that her job was much bigger than her personal life in a sense.

If she took five minutes out of her life to weep over her failed marriage with Matt, then that's five minutes breathing space for Damon or some other criminal to cover their tracks and disappear for good. Elena's job was to put criminals behind bars, and she was pretty damn good at her job too. Her record was squeaky clean with the exception of Damon Salvatore, but soon, she'd also be adding his name to her list of convicted criminals. He was bound to slip up soon, he wasn't inhuman.

He made mistakes too and she had to make sure she was there breathing down his neck when he did. After all, she can't be there to catch him when he does, if she's at home crying into a tub of ice cream over losing the man she loved.

The best way to probably describe her and Matt's relationship was that he was her high school sweetheart. They met in sophomore year when his family moved to her small town of Mystic Falls and it didn't take long for them to become best friends. For a year they skirted around each other as best friends, growing more and more attracted to each other as the days passed. Then in Junior year, Matt had finally plucked up the courage to ask her out and they'd been together ever since, until now.

They sailed through the rest of high school happily together and when Matt learnt that Elena wanted to study in New York, he switched universities to study law and they began their new life in the Big Apple. Elena thought that she was going to spend the rest of her life with Matt, that was until she found him in bed with one of his associates April, one day after she came home early from the office.

Shaking her head and pushing the memories of her and Matt's relationship to the back of her mind, for when she had a private moment, she picked up her car keys. Locking the door and climbing into her Ford Taurus, Elena made it to the FBI headquarters quicker than expected. It probably had something to do with the desire to work that was bubbling up in her stomach, she needed that distraction now more than ever to take her mind off her shitty personal life and work seemed like the perfect solution.

The bulky security guard, Kevin buzzed Elena past into the elevator as she gave him a small smile in appreciation. On the ride up in the elevator, she fidgeted with the classified folder in her hands. The folder that held information on a new con-artist that was making his way around New York, albeit not very discretely. Hopefully, when she presented the folder to Elijah, he'd let her take the case. Elena was fed up of trying to catch a ghost. She needed a case that she could solve. A win.

The elevator tolled it's arrival at the twenty-second floor and Elena walked out as the doors slid open with a bounce in her step. She was completely confident that Elijah was going to let her take this case. After all, she hadn't heard anything concerning Damon in weeks so she could only assume that he was laying low, which meant that they had no chance of finding him at the moment.

"Elena, thank god you're finally here!" A dark-skinned woman exclaimed as Elena walked out of the elevator.

"Why, what's wrong Bonnie?" Elena asked, Bonnie's voice making her nervous. It must have been a damn good reason if Bonnie of all people was on edge. She was usually as cool as a cucumber.

"It's Damon. He's in New York."

"What? Why didn't anyone tell me?" Elena snapped a little too harshly at her friend. The fact that Damon was even in America was a miracle, let alone New York. The last that they'd heard of him, he was in Istanbul and by the time they could react to it, he'd already relocated. While Elena was glad she'd finally have a shot at catching him, she couldn't help but wonder why exactly he was in such a high profile city if he was meant to be laying low and trying to avoid them. Especially the city where the main F.B.I Headquarters of the White Collar division was set-up in.

"He was spotted in JFK Airport last night by their CCTV cameras. But the facial analysis only came in ten minutes ago, I was just about to call you."

Elena sighed and mentally kicked herself for blowing up on Bonnie. "I know. I shouldn't have doubted you and I'm sorry for snapping, Bon. It's just this is our chance to get this son of a bitch behind bars. Could I see the photo that CCTV brought up, please?"

"Sure here you go, 'Lena. Don't worry about it hun. I get it, after two long years were finally gonna nail this guy!"

Unable to contain her excitement, Elena matched Bonnie's bright smile with one of her own. This was it, after two long years on a wild goose chase after a man who seemed almost impossible to find, they finally had the chance to catch him. It almost felt surreal, like she was dreaming. Elena looked down to the photograph that Bonnie handed her, it was almost unfair really that a criminal like Damon could be so handsome. The photograph was in black and white but you could still make out his chiseled jawline and that incorrigible smirk that she'd seen plastered on his face in so many pictures before.

He was dressed in a pair of jeans and a leather jacket with a 'New York Yankees' baseball cap that was impossible to miss on top of his head. Over the two years that Elena had been chasing Damon, if there was one thing that she'd learnt about him, it was that he was the most arrogant man that she'd ever seen in her life and she couldn't quite figure out whether the baseball cap was just because he was excited to be back in New York or whether he was taking a small jab at her. She liked to think the latter though; he was in her city after all and this was probably just another twisted way for him to taunt her. It sure as hell looked like he wanted Elena to know that he was in New York, with the way he was looking directly at the cameras with that annoying smirk of his. It sure as hell wouldn't be the first time. They'd been stuck in this dance for the past two years, trying to stay one step ahead of each other.

"Donovan, get in here!" Elijah called from outside the conference room, his familiar British accent echoing through the busy floor.

As Elena walked to the conference room, she was finally able to observe the rest of the floor. It was in utter chaos with everyone rushing around in what she assumed was to prepare a manhunt for Damon. Everyone in the White Collar division seemed motivated to help catch the man who had evaded them for the past four years. Hell, there were probably people who had been here longer than her that wanted to see Damon brought to justice even more than she did.

Elena walked into the conference room and shut the door behind her. Inside the room were the usual team of Bonnie, Caroline, Klaus and the new guy, Mason. There were also a few others in the room dressed in US Marshal uniforms but she already expected they would be here, this was a city-wide manhunt so of course the US Marshals were going to be informed about the situation. She sure as hell wasn't going to let them take the credit for this bust though, Damon Salvatore was all hers.

"Right then, now that you're all here. As many of you know, Damon Salvatore was spotted at JFK yesterday. Now, judging on past experiences with him, we have roughly a seventy-two hour window to catch him before he disappears again, possibly for good." Elijah informed everyone, his voice taking a rather unusual professional tone to the laid back one he usually used, which probably had something to do with all of the US Marshal's in the room.

With a click of a button on the remote he had in his right hand, the electronic whiteboard on the wall sprung to life with two different pictures of the man in question staring back at them. On the left was a photograph taken in color, obtained from a source that they acquired a while back, one that used to hang around in the same crowds as Damon. While on the right was the picture taken from the CCTV cameras from the airport yesterday.

Elena looked at the picture of Damon on the left. She quickly came to the conclusion that black and white photographs didn't really do the man justice. His onyx, black hair was dishevelled and looked messy, almost as if he'd only just gotten up from out of bed and even in the photo you could make out just mesmerizing his eyes were. That along with the chiseled features and the faint stubble that ran along his jaw made him a sight to behold. It was too bad the guy was a criminal.

"Thanks for the pointless introduction, Special Agent Smith. But we already know who this asshole is, so if you could just step aside and let me and my men take care of this mess so we can all go home to our loved ones, that would be much appreciated." A blonde man interrupted arrogantly as he stepped forward, his US Marshal badge glistening in the sunlight that radiated through the windows and Elena found herself struggling not to roll her eyes at the guy.

He was the typical US Marshal who thought that they owned the place.

"That's a generous offer John, but Elena has it covered. Damon's been her case for two years, you're here for backup if you remember correctly." Elijah replied smoothly, effectively stunning the blonde man into silence.

Elena didn't know who this John guy thought he was, going up against Elijah like that. He wasn't head of the White Collar division for nothing. While he was calm and collected now, Elijah was known to be a man that you didn't mess with as Caroline had explained to her the day she transferred from Washington.

"Exactly! Two years and she still hasn't gotten the job done." John protested and Elena thought that it was about time that she stepped in to show him who was the most prepared to catch Damon. Sure she'd been chasing him for two years and she'd hit dead end after dead end, but she did pick up a few things about him in the meantime. She was certain that she knew more about Damon than anyone else in the building.

"Okay then, John. If you think you're more informed to catch Damon Salvatore, where's the first place that you would look for him?" Elena asked sweetly, trying to keep the malice out of her voice. Who could seriously blame her though? The guy was trying to kick her off the case she'd worked her ass off for two years for.

"Start with seedy motels obviously. The guy's on the F.B.I's Most Wanted List, he's going to want to stay out of the public eye and in the shadows." he replied, an arrogant smile plastered on his face, his whole body language screaming confidence.

She had to admit that if this was any other criminal, that would be the first thing that she would probably do as well. But this wasn't just any criminal, this was Damon. He was cocky and he sure as hell wouldn't stick to the shadows, he'd be wining and dining at the most expensive restaurants just to piss her off. He'd probably sent her photographs of it all as well the arrogant bastard.

"First of all, let's try to ignore the fact that there are probably at least one hundred 'seedy' motels in New York, not only do we lack the resources to cover every motel, it would also be a waste of time." Elena informed, a little too smugly for her own good but who cared, the guy deserved all the embarrassment he got for doubting her.

"And why's that, Agent Donovan?" She could practically hear his teeth grinding together in frustration as he bit the words out.

"Because while we're searching the underbelly of Manhattan's accommodation, Damon is going to be laughing at us as in five star hotels like the Four Seasons."

"Don't be absurd! Those types of hotels have ID scanners, so any fake ID he tries to pass off as his own will be denied. Not to mention his photograph is all over the New York Times!"

"You're underestimating him, John. He's a forger. A perfect one at that, possibly the best. He forged Raphael's 'The Deposition of Christ' and it took our specialists months to find the small, significant detail separating it from the original. Would you like to know what it was?" Elena asked rhetorically, mostly because she just wanted to get her point across as quickly as she could. "His signature. He signed the damn thing. Trust me when I say this... Damon could make a perfect passport or driver's license in his sleep."

Elena watched as several emotions passed over his face before his stern expression quickly returned. Hopefully that would be the end of it, she had proved to him that she knew more about the case than he did; knew more about Damon than he did. John had no chance in hell of taking charge of this case anyway, it was an F.B.I investigation after all. She had no idea why he was being so difficult.

"Look. I couldn't care less about any of that art crap that you guys specialize in. It's my job to catch criminals and If I'm not mistaken, it was you guys who called us." he replied, that massive ego he had making another appearance.

"Yes, we called you in because Damon's evaded us for years and this is probably the only chance we'll have to ever catch him. So we need the extra man power. But don't think for a second that you know this case better than I do!" Elena forced a smile. Her patience with him was really wearing thin. With the morning she'd had and now this guy showing up acting as the be all and end all, the urge to punch someone was overwhelming her. It wasn't even midday yet and she could already tell that she was going to need a drink or two by the end the day.

"Fine have it your way! But if he escapes again then it's on you guys, not us." he sneered before storming out of the room, followed by the other US Marshals in the room.

"Wow Donovan, who knew you had such a bitch streak in you!" Mason chirped in as they left the room, leaning back in his chair with a shit-eating grin on his face.

"You haven't seen anything yet, Lockwood." Elena snapped, not the mood for Mason's snide remarks.

She hadn't known Mason for that long, but in the time that he'd transferred over to this division from Boston, she hadn't really taken to him. He was a good agent, reliable and quick on his feet but the way he held himself in such high esteem irritated her a little more than she cared to admit. It wasn't that she didn't like him. He was just the type of guy that she could only take in small doses before he started pissing her off. Not to mention that he thought he was God's gift to all women.

"Well if you weren't such a dick all the time, she would." Caroline replied, coming to Elena's defense.

"Oh bite me, Caroline."

Elena tried her best to zone out of another classic Mason and Caroline argument and turned towards the window. The view from the conference room was spectacular and as she looked down to busy street below which seemed to be full of life, she couldn't help but ponder that Damon was down there somewhere. He was back in the city, but that didn't exactly narrow down his location. Manhattan was huge, let alone New York. He could be anywhere...

There had been so many missed calls between her and Damon that she was more than determined to catch him this time. Even though she wouldn't admit it, the one advantage that they did have over him were the US Marshals. If they could find his location, it would be near impossible for him to slip them with the whole F.B.I White Collar Division and United States Marshal Service breathing down his neck. Maybe a stroke of luck was in their favor for once, maybe all of the hard work Elena put into this investigation would finally be worth it.

* * *

By time four in the afternoon came around, Elena was seriously contemplating banging her head on the desk repeatedly. After hours of checking CCTV cameras, re-visiting past accommodations that he'd used and running his aliases through their systems, they'd still come up with nothing. She was starting to second guess whether Damon was actually in the city or whether the guy in the pictures was just his doppelganger or something, because there was absolutely no sign of him anywhere in the city whatsoever.

The stress of the whole operation was starting to get to her, not that she would admit that out loud though. If she of all people, for one second admitted that she was slowly losing faith in finding Damon, then what kind of effect would that have on the rest of the team?

She couldn't think like that. This was her operation and she'd be damned if she let anyone else in the division see her sweat.

"Elena! Atticus Shane just called, apparently someone broke into his private vault. It could be Damon?" Bonnie breathed out as she came bursting into Elena's office.

Atticus Shane was the CEO & Founder of Shane Enterprises, a pharmaceutical company that was apparently on the verge of creating a new vaccine that could battle various illnesses in foreign countries. He'd made millions of dollars over the past few years producing various medicines and sprouting other theories that were apparently going to make the world a better place.

To the outside world he looked like the perfect golden boy, the journalists only praised him as they couldn't dig up any dirt on him but the F.B.I knew better, the guy just had one hell of a PR team.

About a year ago, they caught wind of a money laundering scam that was rooted deep within Shane Enterprises. One of the companies' employees came to us when she uncovered the scam while going through the financial records. They sent Caroline in undercover and aside from the fact that Shane repeatedly came on to her, she found a small amount of evidence that indicated the possibility of Atticus himself being the one guilty for laundering money out of his own company's charitable funds.

Unfortunately though, they had to pull Caroline out of there when her cover was close to being blown. Within a week, Shane Enterprises underwent 'staff inspections' and their other inside woman, the one who found the scam in the first place was conveniently fired from her job due to apparent 'budget cuts', leaving them with a nice brick wall in their faces and having no choice but to close the investigation temporarily.

So yeah, to hear that Atticus Shane had millions of dollars potentially stolen from him didn't bug Elena as much as some people might of thought.

"It's definitely him!" Elena announced, rising up from her chair and quickly picking her blazer up from the desk. She was more than ready to head straight over to Shane Enterprises to get some answers. She didn't know why, but she had a distinct feeling that this was Damon Salvatore's handy work. It fit his M.O. perfectly. Damon liked a good challenge and if the rumors that she heard about Shane's personal office from when Caroline was undercover were true, breaking into his private vault would definitely be the type of challenge that Damon would thrive on.

They were out of the office faster than lightning as they began descending the small set of stairs that led from Elena's office to the rest of the floor. They were almost at the elevator when a bubbly, loud voice screeched through the whole floor, bringing them to a stop right in front of the doors.

"Elena, wait!"

Elena spun on her heels to face the perky blonde that was approaching her, a smile on her face that could light up the whole of Manhattan. "What's up, Caroline?"

"We literally just got the weirdest call ever. Some anonymous woman called and said she knew exactly where Damon Salvatore was. She gave us an address and everything..." the blonde quickly unravelled and with the speed that she was talking at, Elena barely caught Damon's name being mentioned.

"Caroline, slow down! What did you say about Damon?"

"We have a potential location."

Although Elena had her suspicions about the anonymous phone call they received, she didn't stop for one minute to question if the information was reliable. There just wasn't enough time. Besides, what were the chances of someone calling about Damon, on today of all days anyway? As soon as Caroline told her the address, Elena rounded up the team and assigned everyone a key role in the take-down.

Mason was quickly on the phone to the US Marshals, making sure that they were at the F.B.I's or rather Elena's command. By time everyone was geared up and ready to go, it was the biggest man-hunt that the F.B.I White Collar division had assembled in over twenty years.

They were pulling out all of the stops to make sure that the investigation didn't go south. Elijah had made a few calls to a few friends of his in NYPD and had somehow managed to create a roadblock on all of the main streets surrounding the address. Although they were careful not to place them too close to the apartment Damon was holed up in otherwise he'd be able to sniff them out immediately.

While some people probably thought that all of the extra precautions that they were taking were ridiculous to say the least, but four years of evading the F.B.I while being hunted relentlessly made these precautions necessary. Facts didn't lie and Damon's track record with them was impressive. Impressive enough for Elena to pull out all of the stops to ensure that he didn't slip through her fingers again. If this mystery woman's information was correct and Damon was where they thought he was, then that meant he wasn't expecting them.

Damon's pattern was usually one in which he kept moving about until he knew he was safe. After that, he usually kept a low profile for a while, and that seemed exactly what he was doing now. In a few hours, word of Atticus Shane being robbed would hit the news nationwide and the whole city would be thrown into a frenzy as to why the city's golden hero was robbed. Shane had friends in high places; he probably had enough power to have the most of the NYPD helping him if he wanted.

Now if Elena were in Damon's shoes, she'd probably lay low for a while until everyone were distracted enough with the news about Shane before making her escape.

So if Damon was staying in one spot, that meant he thought he was safe, untouchable. Which meant that for once, Elena had the jump on him.

But if this whole operation went sideways, then she had a feeling that he would disappear for good. With how fast they caught on to him when he arrived back in New York, he wasn't stupid enough to come back if he somehow managed to escape today. Elena couldn't help but fear that if they lost him today, they'd lose him forever.

Once everyone knew their role, they were soon on their way to the address that they were given. Elena's hands were clammy as she tightened her hold on the steering wheel, a nauseating feeling brewing in the pit of her stomach. This was it. Two years of hard work and dedication, a small promotion and a failed marriage later and she was finally on the verge of catching her man. The sudden realization was both terrifying and exciting at the same time.

Elena came to a stop a block or two away from the building that Damon was meant to be in. She thought that it was probably best that they moved in on foot to reduce the chances of Damon catching on to the fact that they were closing in on him.

As they approached the block of apartments that Damon was meant to be holed up inside of, Elena raised her fist in the air, motioning for Bonnie and the small group of F.B.I agents behind her to stop. She reached inside her blazer and pulled her Glock 21 handgun out of her holster. She knew that Damon wasn't known for using firearms or other weapons but she couldn't take the risk. If he tried to run or attack them, she wouldn't hesitate for a second to put a bullet in his leg.

Elena couldn't stop her heart from beating a mile a minute as she ascended the stairs and stealthily made her way to apartment room 2AB, the room that Damon was apparently in. She paused for a second as her hand rested on the door handle and looked to Bonnie for a moment. Her friend shot her a small, encouraging smile before nodding her head to the handle. Surprisingly, the door was unlocked and Elena used the weight of her shoulder to swing the door open. Immediately she raised her gun in front of her and crept through the hallway, the small team of F.B.I agents following behind her.

"It's about time you lot got here." A velvety voice echoed through the apartment, startling everybody into raising their guns towards the source of where the voice was coming from.

They carefully approached the room, keeping their guns firmly aimed in front of them. The suspense was starting to get the better of Elena as she started moving quicker and quicker to the entrance of where the mysterious voice originated from. When she finally made it to what she supposed was the living room of the apartment, a small flicker of a switch engulfed the room with light, disorientating her eyes for a quick moment.

Once her eyes adjusted to the blinding light, she quickly focused on the dark haired man sitting on a chair in the middle of the room. She quickly took a sharp breath of air as she finally laid eyes on the man who she had dedicated the last two years of her life to. A man who was essentially a stranger to her. But yet, as she stared into the most incredible oceanic blue eyes that she'd ever seen before in her entire life, she felt as though she'd known him for a lifetime.

"I guess this would be a bad time for me to ask for a cigarette, huh?" The man slurred slightly as he raised a glass to his lips, downing an amber liquid of some sort.

"Put your weapons down guys." Elena replied, holstering her handgun. He was clearly not in a state to struggle against them so there was no point in making this uncomfortable for him with about fourteen different guns pointing in his face.

The man's eyes zoned in on her and as they took in the sight of her, Elena felt herself feeling very uncomfortable with the way he was staring at her as if she was a piece of meat and the hairs on the back of her neck standing to attention. The man slowly stood up from the chair, using the armrest to help balance himself when he almost fell back down. He swayed slightly on his feet before holding his hand out to her with an incorrigible smirk on his face.

"Elena Gilbert, I don't believe we've had the pleasure of meeting before. I'm Damon."

* * *

_**AN: **I hope you enjoyed the first chapter. I would really appreciate if you guys let me know if you think I should continue with this :)_

_For those who follow my other story "Fate Brought Us Together". I've not abandoned that story at all, I've just hit a few roadblocks in planning out the upcoming chapters and seeing where I want to take the story, a sort of writers' block. But don't worry too much, you shouldn't have to wait too long for an update as I'm halfway through the next chapter and I should be well on my way to finishing it soon._

_Also, you can check out my twitter for news on updates as well as other ramblings about stuff if you want. You can follow me curiouswriter1_

_Until next time,_

_xox_


	2. Chapter 2

_**AN:** I'm so overwhelmed by the positive response to this story so far, so thank you all! There's a bit of a time jump in this chapter from the first one, but I think that it was necessary one to have. Before we get into this chapter though, I'd just like to say that I am in no way an expert on priceless art or committing crimes for that matter so while I do research what I am writing, It's mostly going to be fiction and I'm most likely going to be inaccurate on some things so if that bothers you, I'm sorry for that and hope it doesn't put you off the story._

_A big thank you to me beta cdaye8184 for making sure that this chapter was good enough to post. She's awesome._

___This story is inspired by the television shows White Collar & The Vampire Diaries._

* * *

**Uncharted Waters**

Chapter 2

_"I've dreamt about you nearly every night this week,  
How many secrets can you keep?  
'Cause there's this tune I found that makes me think of you somehow and I play it on repeat,  
Until I fall asleep,  
Spilling drinks on my settee"_

_Do I Wanna Know? - __Arctic Monkeys_

* * *

**Three Years Later**

Elena rested her head in the palms of her hands, exhausted from the past twenty four hours. After finally catching Damon and putting him behind bars, Elena's career sky rocketed up within the Bureau. Along with quite a hefty increase in her salary, she was also offered the chance to move up into the Homicide division which was classed as the "big leagues", although she politely refused. Besides the fact that Elena preferred the White Collar division, the Homicide division was a kill or be killed environment, with everyone fighting with each other and stabbing each other in the back for the bigger cases. Elena felt as though she could only trust the Homicide division about as far as she could throw them; unlike the team she had with the White Collar division.

After her divorce with Matt was finalized, Elena changed her surname back to Gilbert and started focusing on her career more. Apart from the occasional blind date set-up by either Caroline or Bonnie, Elena's love life was pretty much non-existent. In fact the only love she had in her life at the moment was her two year old cat, Smithers. She'd found Smithers at an animal shelter about two years ago, after he'd been abandoned by his owners. She guessed that she was still reeling from her failed relationship with Matt and feeling lonely, that she felt having a pet around the apartment would be a good thing.

It turned out that it was in fact one of the best decisions she'd ever made in her life. It didn't take long for her to fall in love with Smithers, although it took a while for him to settle in to her apartment.

The worst thing about her fall out with Matt was that they still sometimes interacted within the same social groups. About a year after their divorce, Matt accepted a job at Federickson & Co. an insurance company which often collaborated with the F.B.I in returning priceless pieces of art. She didn't know if he took the job to keep an eye on her or something like that, but the one thing she did know was that it was awkward as hell when they were in the same room together.

Every time she saw Matt, it just brought up painful memories that she would rather forget and it pissed her off that she had to see him every few weeks. If it was down to her, she'd make sure that she never had to see his cheating face again. Unfortunately for her, she wasn't that lucky.

"Still no luck?" A perky voice called out.

Elena quickly looked up to see her bubbly blonde, best friend staring down at her with concern, "Nope, none whatsoever."

"Maybe you should take a break? Grab a coffee or something 'Lena."

"I'm fine, Care. I just need to crack this one."

Elena stared down at the identical photographs, much like she'd been doing for the past two hours or so. Over the past year, a new forger had made his or hers way across the F.B.I's radar. The only thing they knew about their mystery forger was that they worked in patterns of four months. Every four months they would appear in New York and fence off a priceless piece of art to the highest bidder. Miraculously, the F.B.I had managed to intercept one of the pieces of art by sending in Caroline undercover as a potential buyer.

Once they busted the fence, they retrieved a near perfect forgery of Van Gogh's 'The Red Vineyard'.

The only reason Elena knew it wasn't the original was because the Pushkin Museum of Fine Arts in Moscow, where the original painting was on exhibit, confirmed that the original was still in place. So as Elena stared down at the almost identical photographs of two entirely different paintings, she had no idea where to start. The so called professional analysists at the F.B.I were proving to be useless as they couldn't even identify a difference with the forgery, even the paint and canvas used were from the same year as Van Gogh's.

Whoever this mystery forger was, they certainly liked to be accurate with their details.

"You know, this almost reminds me of Damon Salvatore's work." Caroline noted as she looked down over Elena's shoulder at the photographs.

It took around twenty seconds for her words to sink in, but then it clicked, "Not almost, this is exactly like Damon's work."

Elena couldn't believe that it had been staring her right in the face for so long. The attention to detail, the choice of painting, it was too Damon for her liking. She didn't think it was by coincidence either. She needed to see him, prove herself wrong in thinking that he'd somehow escaped the maximum security prison that she'd left him in.

"Where are you going?" Caroline asked which ended up sounding more like a demand than a question as usual with the bubbly blonde.

"I need to see him." Elena replied cryptically, gathering the files she had on her desk as quickly as she could.

"Who Damon? Come on Elena, do you honestly think this is him?" Elena didn't miss the skepticism in her best friend's voice. It was definitely a long shot, but if there was anything that she had learnt when chasing Damon, it was to never write him off about anything.

"Yes... no. I don't know, maybe? There's only one way to know for sure." She replied while trying to put her blazer on with one arm.

"Here let me help." Caroline said, taking the files from Elena so that she could put her blazer on. "Are you sure about this? Do you want me to come with you?"

"Yes I'm sure. I think it would be best if I went alone though, you need to hold the fort down after all." Elena replied with a small smile.

"But it's Damon..." Caroline moaned in her typical melodramatic fashion.

"Yeah and he's behind bars, in a maximum security prison. I think I'll be fine."

While she knew that Caroline was just looking out for her, Elena knew that Damon wasn't as dangerous as he was made out to be. As she climbed into her car, she quickly entertained the idea of what he looked like now after three years. She'd be lying if she said that Damon hadn't popped up in her mind a couple of times in the past couple of years. Hell, there'd been one or two occasions where he'd _literally_ popped up in some of her dreams, although she'd die before admitting that out loud to anyone.

She wondered how prison might have changed him; if he was still as arrogant as she believed he was three years ago when she caught him. If that sparkle in his blue eyes was still there, or if it had faded over time while living in that hell hole of a maximum security prison. A prison which was made for murderers and rapists, not people like Damon.

It wasn't long before she was parked in Sing Sing Correctional Facility's visiting car park and gathering the files that she needed, ready to question Damon. The last time that she was here, she'd actually been to see Damon. It was a few weeks after she had caught him and she couldn't explain why but she just had to meet the man she'd been chasing for two years, not the drunk she'd met the night she caught him. Of course she chickened out when she got to the front gate but she wasn't about to history repeat itself here.

Once she had the necessary files that she needed to show Damon, she was out the car and on her way towards the entrance. After checking in at the front desk and flashing her F.B.I badge to some people so that she didn't have to sign some visitor's form, she found herself sat in a private interrogation room that she'd managed to occupy, waiting for Damon to be brought out. After a few minutes of waiting impatiently, the lock to the door finally clicked open and Damon emerged through with two guards to the side of him.

Elena was shocked to see how different he looked from the last time she saw him. His obsidian hair was a lot longer, curling around his ears and the once bare jawline was now covered in a beard that matched his hair. The only thing that she could match with that night three years ago, were the same spectacularly blue eyes, which were now spearing into her as he walked through the door. Besides that, it looked as though prison hadn't done Damon any favors which pleased her to a certain extent. Prison was more than what he deserved for all of the things that he'd done.

"Well color me shocked. You're the last person I expected to come visit me, Agent Gilbert." The raven haired man mocked as he was escorted to the chair across from her by two guards. Elena nodded towards the two men, indicating that she wanted them to be left alone and breathed a small sigh of relief when they closed the door on the way out, giving them the privacy that she wanted.

"Believe me, I would rather poke my eyes out with a rusty nail than be here if it wasn't so important that I speak to you." Elena retorted with disgust. Just as she expected, the first words out of his mouth were laced with arrogance. Typical.

She watched as he re-positioned himself in the seat and tilted his head to the side slightly, "What a shame. They're such pretty eyes as well."

"I need you to take a look at these photographs for me and tell me what you know about them." Elena carried on, ignoring his inappropriate remark.

"So demanding... I like it. However, why should I help you? I mean, you never write or call..." He rambled on with an arrogant smirk on his face.

"Stop messing around, Damon. This is important!" She snapped, fed up of his inability to take this serious.

"Oh I'm not messing around, Elena." He simply replied and she hated the way he dragged out every syllable in her name.

"Well, what is it that you want? A razor? You look like you need one."

He chucked before raising his eyebrow, "Cute. But no, I want the same as every man in here, I want out."

Elena couldn't help but laugh out loud at Damon's ridiculous request, "Oh come on Damon, I know for a fact that you're not stupid enough to think that I can just simply set you free." She breathed out between laughs.

"Not free. Into your custody so to speak, well the F.B.I's custody."

"You're insane." Elena muttered, shaking her head.

"And you're delusional if you think I'm going to help you out of the goodness of my heart." Damon deadpanned as he leant back in his chair.

"You don't want much though." She bit back sarcastically.

"That's my offer, Gilbert. Take it or leave it."

"Goodbye Damon." She'd had enough with the ridiculous conversation they were having. He was crazy to think that she would just negotiate some sort of deal for him to be set free just because he gave her a little bit of information on some photographs.

* * *

Elena sighed as she checked herself over in her bedroom mirror. After her conversation with Damon went bust, she went back to the office in hopes of figuring out the case herself, which only left her more frustrated than she was in the first place. Whoever this person was, they were good but the fact that they only popped up on the grid every four months made it almost impossible to figure out who it was.

She needed to know why, but the only way she knew how to find out was sitting in a six by eight prison cell.

After applying some lipstick and throwing her leather jacket on, Elena headed out towards a bar that she and the girls were regulars at. It was only a quick cab ride from her apartment and it wasn't long before she was inside, nursing a glass of whiskey to help clear her thoughts about the whole Damon situation. Elena wasn't your usual cocktail and tequila drinking type of girl, she liked her liquor with more of a kick. While her friends liked their sex on the beaches and their margaritas, Elena liked her whiskeys and scotches.

"So what was it like meeting Damon?" Caroline asked while sipping on a pink cocktail.

Elena took a long gulp of her whiskey, enjoying the burn before replying, "Just as I expected, stressful and I left feeling more annoyed than before."

"It was that bad, huh?" Bonnie asks before taking a sip of her own drink.

"Worse. He's everything I expected him to be, arrogant and sarcastic." Elena unloaded on them.

"Sounds hot." Caroline chirped in quickly with a grin.

"No he's not. He's just so, so... infuriating!" Elena snapped. Damon might be ridiculously hot, beard or no beard, but his personality ruined any attraction she thought she had for him. Not to mention that he was a criminal. She didn't know about Caroline or Bonnie, but 'bad boys' definitely weren't her type.

"Is it possible that we've finally found someone who can go toe to toe with Elena Gilbert?" Bonnie turned to Caroline with a smirk on her face.

"Oh I believe we have." Caroline shot back with a smirk of her own. Seriously, it was like they were symmetrical.

Elena let out a dry laugh, "Pfft, Damon's no match for me girls. Or are we forgetting who caught him?" She giggled before taking another mouthful of whiskey.

"Yeah because you and Damon as _so_ not alike." Bonnie retorted sarcastically and rolled her eyes before bursting into giggles herself.

The rest of the night flew by. Caroline found a group of guys by the bar and brought them over to the table and for the past hour or two, they'd been hanging out and getting to know them. Elena and Bonnie were quite happy to have a girls' night out but as usual with Caroline, she spotted her prey and like the lioness she was, she pounced.

However, Elena's mind didn't stray too far from Damon all night. As much as she would hate to admit, he was their only lead right now and she couldn't see any other way to figure her problem out. It wasn't as if she had a lot of time to sit and think on this either, considering the window to catch this forger was closing rapidly. Soon she'd lose them and whoever this forger was would be gone for another four months. If Elena wanted to close this case, then she needed Damon's help. The only problem was that she didn't think she could let go of her pride and give into his demands. How in the world would she even be able to get him into the custody of the F.B.I anyway? It's not like she could just walk in, snap her fingers and then Damon would be free. Fuck, why was she even considering this?

"Hello, Earth to Elena?" Caroline retorted as she clicked her fingers, snapping Elena out of her inner debate.

"I'm sorry, what?" Elena mumbled on confused. She looked around at the table, all sets of eyes on her as she nervously fiddled with her fingers under the table. She must have zoned out halfway through the conversation again. Her eyes focused in on Caroline, who was sat across the table shooting her a death glare.

"_Harry_ was just talking about how he's just passed his bar exam." Caroline emphasized while raising her eyebrows and she couldn't be anymore transparent if she tried, in her attempts to hook Elena up with someone.

"Oh yeah that's great." Elena replied, disinterested. Oh great, the last thing New York needed was another lawyer.

She knew she was being a little harsh in her assumptions of Harry, but Elena wasn't really interested in dating another lawyer or bedding one for that matter. She'd been there, done that with Matt and it left a bad taste in her mouth after she caught him cheating on her. It wasn't that this Harry guy wasn't attractive or a bad guy or anything, but Elena wasn't really interested in hooking up with anyone when she had bigger fish to fry in her head, much to her best friends' dismay.

"I'm actually gonna head home now, early start tomorrow and all." Elena announced. If she was being honest, she just wanted to go home, curl up on the couch with Smithers and catch up on some television. God knows she wasn't going to be getting any sleep tonight either with everything that was swimming around in her head, so it was the perfect opportunity to catch up on her favorite vampire shows.

"Want me to go with you, hun?" Bonnie asked, her words slurring.

Elena shook her head, not wanting to ruin her friend's night just because she wasn't up for hanging with them and the guys they'd met. She quickly said her goodbyes and planted a kiss on Bonnie and Caroline's cheeks before shrugging on her leather jacket.

She decided that she'd walk back to her apartment instead of taking a cab. It was an extra twenty minutes walking but she didn't mind, she needed to clear her head and some fresh air would do her good while she debated on what to do with Damon. As she walked out the bar, the wind chilled her skin, causing her to zip up her jacket and place her hands deep in her pockets in an attempt to keep her hands warm. As she began walking back to her apartment, she started thinking more about the raven haired man.

Maybe if she went back to the prison, she would be able to convince Damon to help her, without getting him out of prison.

She didn't like the idea too much, but she had no other choice. He was her only lead and she knew that soon, her window to catch her criminal would close and she would be left out in the cold again. As much as it would hurt her pride to go back to him, catching a criminal was more important and ultimately, worth the humiliation that she would face with Damon.

The thirty minute walk back to her apartment went by quicker than she expected and the incessant purring when she unlocked the door to her apartment made her smile. A flash of white sprung out from the hallway as Elena walked into the apartment, shutting the door behind her. It didn't take long for Smither's small frame to be wrapped around her leg and for him to start meowing like crazy as she ditched her jacket on the coat rack. She kneeled down and started smoothing him softly in between his ears. The return of his purring telling her that he'd missed her while she was out.

After feeding Smithers and sitting down on her couch nursing a glass of bourbon for an hour, she finally made the decision to suck it up and go see Damon. Worst case scenario was for him to know nothing while the best case scenario was for him to give her a vital piece of information that she could use in her investigation. She had nothing to lose, except maybe her sanity. After all, she would be spending another afternoon with Damon Salvatore.

* * *

"I knew you'd come back, I just didn't think it would be this soon." Damon remarked smugly as he sat across from her the next day.

"Don't act so smug. Trust me, If there was another way, believe me I'd take it." Elena replied.

The raven haired man only smirked before replying, "And yet here you are, asking me for help."

"Like I said, there isn't another way."

"Okay, okay." Damon raised his hand-cuffed clad hands up in defence, "Like I said the other day; I scratch your back, you scratch mine."

"I'm not getting you out of here just for some information on two photographs, Damon." Elena huffed out with frustration.

"I was thinking more along the lines of I help you catch your guy, or girl for that matter." He quickly fired back.

Elena had to admit that it sounded promising. Damon would certainly be an asset to her if she were to have him working with her to catch this criminal. Although the F.B.I was full of so called experts, there was no denying that Damon's eye for detail was almost inhuman. It also wouldn't hurt to have someone who was experienced and had the mind set of someone who has been on the other side of an investigation helping them out.

"Hypothetically now, how would we go about this?" Elena asked cautiously.

"Don't you guys have like consultants or something that help you out? I can be yours." He said with a small shrug.

"Oh yeah? And for some reason I doubt whether you'll even stick around, I wonder why that is?"

"Simmer down, Sassy. That's easy enough; tracking anklet, I heard the latest model is unhackable." He replied effortlessly and Elena struggled not to flip him and his self-absorbed, know-it-all self off.

"You seem to have this all figured out." Elena noted.

He quickly leant forward, resting his elbows on the table and clasping his hands together while he inched closer to Elena's face, "Isn't that why you wanted my help in the first place? I have everything figured out, Elena." He whispered into her ear, sending tingles up and down her spine, effectively turning her cheeks crimson. Jesus, suddenly she was feeling a lot hotter than she was before.

"I-I just don't know if this is a good idea." She mumbled, more to herself than Damon.

His face softened a little as he stared at her, "Sometimes, Elena. You've just got to take a leap of faith."

A long silence stretched over them as Elena contemplated Damon's offer. She'd never really entertained the idea of having a consultant before. Never thought she needed one. She looked up from her hands at Damon, his piercing eyes staring into her and the only thing she could compare it to was the night she caught him. The intensity was overwhelming and while she knew this would probably end up being one of the worst decisions that she'd ever make, she went ahead and made it anyway.

"Okay, fine. But I swear to God if you screw me over Damon, I'll come down on you like a ton of bricks. Are we clear?" Elena warned, her resolve slipping as she gave into her own insanity.

"Crystal."

* * *

_**AN: **I hope that you enjoyed this chapter. Damon and Elena don't really like each other much at the moment, do they? ;)_

_I'd just like to take the time to thank everyone who has followed, favorited and reviewed the Uncharted Waters. It was a real relief that so many of you liked the idea of a White Collar spin on things, because I honestly thought not many people would be interested. I'm also going to be getting around to replying to some of your reviews, once I have a bit of spare time so just hang in there for a little while longer please._

_Twitter: curiouswriter1_

_Until next time,_

_xox_


	3. Chapter 3

_**AN: **The support for this story just continues to amaze me! 40 reviews for just two chapters is brilliant and I'm so thrilled so many of you love the story so far._

_This chapter hasn't been beta'd so if there are any mistakes or if the chapter just sucks then yeah, it's my fault and I'm sorry._

___This story is inspired by the television shows White Collar & The Vampire Diaries._

* * *

**Uncharted Waters**

Chapter 3

_"I'm waking up to ash and dust,  
I wipe my brow and I sweat my rust,  
I'm breathing in the chemicals,_

_I'm breaking in, shaping up, then checking out on the prison bus,  
__This is it, the apocalypse,  
__Whoa"_

_Radioactive - Imagine Dragons_

* * *

Elena drummed her finger on the steering wheel as she sat parked outside the Sing Sing Correctional Facility. After her third visit to the facility within a week, she was really starting to get sick of seeing the place and hopefully after today, she wouldn't have to see it for a very long time. Another five minutes quickly passed and Elena was really starting to wonder where the hell Damon was. She was told to be here for ten to pick him up and it was now half past, but there was still no sign of him.

She was just about to get out of the car and go see where he was when the front doors to the facility opened, revealing the man in question himself being escorted out by a security guard twice the size of him. Elena used the few minutes she had in the confined safety of her car, shielded from prying eyes, to quickly check Damon out. Although his hair was still fairly long, he'd finally shaved that god awful beard that he'd been sporting the first day she met him and she quickly decided that a clean shaven Damon was much more attractive than a caveman one.

The orange jumpsuit had also been replaced by a pair of dark wash jeans and a black v-neck, accompanied by a dark grey servel jacket and a pair of black boots to match. He was also wearing a pair of sunglasses, which was freaking ridiculous considering it wasn't even that sunny outside, like seriously! It was hard to imagine that he was only just coming out of prison, considering he looked as though he was stepping out onto a freaking photo-shoot!

She watched as he flashed the security guard a smile before making his way over to the car, sauntering towards her like they had all the time in the day. While the guy was extremely cocky, she had to admire him a little for the way he held himself. He was strutting towards her like a peacock, he was obviously comfortable in his own skin and rightly so. His whole demeanor just screamed sexy and confident, which not many people had the self-esteem to pull off.

"Where the hell have you been?" Elena asked in a not so polite way as he climbed into the car. So what? He deserved it.

"Hello to you as well, Elena." Damon replied, readjusting his sunglasses before throwing her a loop-sided smirk.

"I've been waiting here for thirty minutes." She deadpanned, not happy about the fact she was forced to wait in her car for half an hour.

He sighed, "Jesus take a chill pill, 'Lena. You'll burst a blood vessel or something. There was just a little bit of difficulty putting this clumpy thing on, that's all." He said as he quickly exposed his right ankle, showing off the new addition to his body for the next couple of years.

She ignored his use of her childhood nickname for a second and focused in on his ankle. The sight of the black tracking anklet on him replaced the frustration she was feeling for him with a small dose of joy. She bit her tongue, stopping her from pointing out the fact that he was basically her little bitch for the foreseeable future and put the car into drive silently.

They'd only been on the road for about five minutes before he opened his mouth, ruining any chance of peace that Elena thought she'd get.

"Where are we going? To the secret headquarters?" He mocked, waggling his eyebrows.

She grinned at the thought of where they were really going. She was sure that he'd have the shock of his life when she introduced him to his _spectacular_ new living requirements.

"Something like that." She replied cryptically. She wanted to keep where they were actually heading a surprise.

They soon drifted off into a comfortable silence as they made their way back to Manhattan, the only noise filling the car was the soothing sound of Taylor Swift in the background. She liked to dabble her music tastes and she found that Country music really relaxed her when she was driving, which wasn't and easy task to do. Ever since her parents' car accident when she was younger, she wasn't really comfortable in and around cars but they were necessary in such a big city like New York. The fact that Damon also had a massive scowl on his face as Swift's lyrics blared through the speakers made her feel a lot better.

"That's it, I've had enough of this crap." Damon whined as he reached for the radio.

Before she could even second guess herself, she gave his hand a quick slap before he could change the channel, "What's your problem, Gilbert?" He questioned as his hand recoiled, his ice cold eyes scolding her as if she were a child who'd done something wrong.

"My problem is you trying to change the channel on _my_ radio." She fired back quickly, avoiding his steely gaze and keeping her own on the road.

"Are you deaf? This music sucks."

"Well why don't we both just jump into your car, then you could pick the music. Oh wait, you haven't got one. Why? Because you've been in prison for the last three years."

"Yeah well prison seems a lot better than here right now."

Elena growled a little as her frustration with the man beside her grew, "Why did I even agree to this in the first place?"

"Because you actually want to solve some cases?" He retorted sarcastically.

"I'm sorry, what did you just say?" She asked hysterically, almost swerving the car into the opposite lane while doing so.

"Did I stutter or something?"

"Well I caught you didn't I?"

She watched in satisfaction as he faltered slightly. Of course though, it didn't take long for him to recover before his lips spread out in that unbearable smirk that was quickly becoming a trademark of his.

"Hmm, touche Gilbert." He replied, his eyes gleaming as if he secretly knew something that she never.

* * *

"You've got to be kidding me." Damon mumbled to himself as he took in the rundown building.

"Nope, this is where you're staying." The brunette to his right replied with a bright, condescending smile.

He had to admit, he quite enjoyed this little sparing match that they had going on. He knew all the buttons to press to rile her up and he found that she was slowly starting to find her own buttons to use against him as well. She was a feisty little thing, a stubborn one as well. He now understood how she was so relentless when she was chasing him. It had been a long time since someone had challenged him the way Elena had and it was quite frankly... a turn on.

He'd always liked women who took charge and knew what they wanted and Elena Gilbert was no exception. In the brief conversations that they'd had over the past week, he quickly figured out that she was very committed to her job and she didn't like to lose. That was easy enough though, she wouldn't have come to him so desperately if she didn't want to catch her guy.

Of course, that wasn't the only thing that he'd noticed about her in his observations. The girl was a knockout, she was drop dead gorgeous. Her big brown eyes fit her heart shaped face perfectly and if he wasn't careful, those doe eyes of hers would start causing him more trouble than he thought. They definitely held the power to bring a man down to his knees. Her wavy, maroon locks complimented her olive skin tone beautifully and the curves of her sinful body which were highlighted by her tight-fit suit, left him imagining what it would be like to undress the goddess before him and ravage her until their muscles ached and burned.

Holy shit it had been _too_ long since he'd taken part in that type of physical activity.

"Jesus it won't bite, Damon. Stop being such a wuss." Elena snapped, holding the door open to the seedy motel for him.

He quickly recovered from his blatant staring, "Something tells me you like to bite though, Elena." He purred as he brushed past her.

"Wouldn't you like to know." Damon couldn't help but gawk as Elena pushed past him to the front desk with what he assumed was a playful smirk on her face.

Fuck! Elena one, Damon zero.

After checking in with reception and receiving the keys for what was supposed to be his new "home", they slowly trudged up the creaky, metal stairs to the third floor. He held onto the staircase banister as they climbed the stairs, not taking comfort in the fact that the whole building felt unstable. He'd stayed in some pretty shit accommodations in his time on the run but this one certainly took the cake, and he hadn't even seen his room yet. Flies kept buzzing around his face and the place also had that distinct hospital smell that he hated.

Once they made it to his room, Elena unlocked the door and pushed it open, revealing the small room that he was expected to live in for the next few years.

"Home sweet home." Elena said enthusiastically, clearly a lot happier than he was about the living arrangements. Yeah, she was milking this up.

"My prison cell was cleaner than this." Damon noted as he scanned the interior of the room.

The room was your typical motel one, a singular bed in the corner of the room next to a bedside table. He'd bet his freedom that there was probably a small Bible in the draw as well. The flowery wallpaper was worn, even shredded in some places on the walls. It was probably around ten years old, not that he thought the motel would replace the wallpaper anyway. He gingerly stepped inside the room, taking in the rest of the surroundings. The hospital smell was gone, replaced with a sewery stench that was debatably worse.

"I'm not staying here." He quickly announced, disgusted by the state of the room. No, he would rather die than stay here for a night, let alone a few years.

Elena sighed, noticing the determined look on his face, "Look Damon. On the two hundred and fifty dollars a week the F.B.I are giving you, this is the only place you can afford."

"What if I told you that I already had an apartment smack dab in the middle of Manhattan?" Damon questioned reluctantly after a minutes silence. He honestly didn't want to expose the only place he'd felt safe in to Elena, but it was better than spending the next couple of years living in a shit hole like this.

"Has it been bought legally?" She replied squinting her eyes at him, suspicion rolling off her in waves.

"I bought it nine years ago." He answered, telling her what she really wanted to know - If he bought it with money that technically wasn't his. As far as he was concerned, the F.B.I were unaware of anything he'd done before he popped up on their grid seven years ago.

"That doesn't mean anything Damon and you know it!" She fired back quickly.

"Shouldn't we get going instead of wasting our time here? You know, baddies to catch and all." He deflected effortlessly with a smirk. Judging from her piercing glare though, he knew she wasn't going to drop this conversation anytime soon.

There was an awkward silence as they left the shady motel and traveled to their next destination, Damon only speaking to give Elena directions to his safe haven. There was no going back now once he walked inside the apartment he'd had for so many years, yet never exposed to anyone before. There was only one other person who knew that it even existed and he was nowhere to be found. But now he was risking it all for a woman who'd sent him to prison.

"Make a right turn by here." Elena quickly followed his orders, turning down into the underground car park of the apartment block. "Stay here a second."

He glanced at her quickly as she gave him a quizzical look before he climbed out the car. The car park was filled with various different cars, but he only needed one. A light blue 1969 Chevy Camaro. Without the car, he wouldn't be able to get into the apartment, which would mean a one way ticket back to that pathetic excuse of a motel. Damon couldn't stop the Chesire like grin forming on his face as he spotted the Camaro in the corner of the car park, trapped between two cars.

"Bingo!" He murmured to himself, quickly making his way over to the only car he'd ever bought in his life. His baby.

After checking to see if anyone was watching, he carefully knelt down and reached into the front wheel. It took him a good few seconds of fiddling around the rim of the tire before he finally found what he was looking for - his apartment keys.

* * *

Damon walked over towards her with a smug grin on his face, pissing her off even more. She'd only spent the past couple of hours with him and she was already preparing to throttle him. This plan of hers was beginning to bite her in the ass more and more as the minutes passed. Damon had been out of jail less than a day and he'd already set off some red flags in her head that she couldn't ignore. Not to mention that they'd checked all properties owned by Damon when they were chasing him three years ago and this place certainly hadn't come up. There was definitely something suspicious about this apartment he had and she was going to get to the bottom of it!

"What the hell are you doing?" Elena demanded furiously as she climbed out the car. She was tired of this little goose chase that he had them doing.

"Getting these bad boys." He replied wearing a coy smirk and dangling a pair of keys in front of her face.

Elena quickly looked around to see if anyone was there before interjecting, "Damon, what are you doing? You can't just steal someone's keys! It's like you want to go back to prison." Was he really stupid enough to pull something like this right in front of her?

"Relax princess, they're mine." He assured her while she fell into step with him as they started walking to the elevator on the other side of the car park.

She breathed a small sigh of relief before snapping her attention back to the infuriating man in front of her, "Don't call me that!"

"Call you what?" He replied feigning innocence.

"That... _that_ word!"

"You need to take that stick out of your ass, Gilbert. Most girls would be pleased with a guy calling them _that_ word." Damon mocked

"Yeah well there's a big difference between a guy calling me princess and a convicted felon."

"Still hanging on to that are we princess?"

"God you're insufferable!" She exclaimed as they entered the elevator.

They fell back into that silence that Elena was already too familiar with. This seemed to be how they operated, she mused. They'd act civilized with each other for all of about five minutes before Damon made some kind of innuendo or made some irritating comment that just set her off, which then resulted in them bickering. She had no idea how they were going to work together. Hell, she didn't even know if she was going to get through the rest of the day without killing him or sending his ass back to jail.

It certainly didn't help that they seemed to have a sort of connection that she'd never felt before with anyone else. You could feel it when they were arguing, the tension between them was electric, with an underlying of sexual attraction, at least on her end, that magnified things ten fold. Not that she would ever admit it, those were her private thoughts. Ones where she wouldn't be scrutinized or laughed at for even thinking. Besides, it's not like anything would happen. She would definitely not let any supposed connection that she thought they had blind her in any way, and she would definitely _not_ go there with a conman like Damon, ever.

The elevator doors opened and they both stepped out into the reception area of the building. She followed him out as he walked to the reception table where an old woman who looked to be in her 60's with black-rimmed glasses sat.

"Good afternoon, Brenda." Damon smiled and Elena was shocked at the genuine warmth in his voice.

"Mr Hunt is that you? I thought you fell off the face of the planet." The old woman chuckled as she quickly rounded the desk and pulled him into a bear hug.

Mr Hunt? Who the hell is... oh wait, of course. Another alias.

"Unfortunately I haven't." He smirked before continuing, "I've just been... travelling." He finally replied. _Yeah travelling my ass!_

"That sounds wonderful dear! And who's this beautiful young lady?" Brenda asked sweetly, turning her attention to Elena.

"Oh I'm his handler." Elena smiled brightly, extending her hand out to the woman. Yeah... he wasn't going to get away with flashing his baby blues and tricking a poor woman into thinking that he was some sort of saint!

"Actually I'm her consultant." Damon intercepted, narrowing his eyes at her.

"Consultant? I thought you were a banker?" Brenda asked confused.

"Yeah, I changed profession. Anyway, I'll speak to you later Brenda, we really need to go." Damon said quickly before taking Elena by the arm and dragging her towards the staircase.

"What the hell was that?" He demanded once they started making their way up the stairs.

"Hey don't be mad at me! You're the one whose lying to an old women!" Elena shot back in frustration.

"Yeah for her own good!" He tried to reason but Elena was having none of it.

"You want to protect her? Well here's an idea," she flared out dramatically, "how about you leave her alone!"

Damon abruptly stopped in the middle of the stairs and spun around on his heel to face her, almost causing her to walk straight into him. Her left hand quickly shot out to grab a hold of the staircase banister, stopping herself from falling. "What the hell!"

She found it impossible to look away as she was met with cold eyes. Their usual shade of blue was darker than she remembered as she peered into them, it was almost as if there were a storm brewing in them. His eyebrows were furrowed as he frowned down at her, making her feel minuscule under his accusatory gaze. She swallowed audibly as she felt a lump forming in her throat. She started thinking that maybe she had overstepped some sort of line, she often had a tendency to say things without really thinking them through. A trait that she most likely picked up from Caroline after being friends with her for so many years.

"I really don't appreciate you butting your nose into things that don't concern you, Elena." He stated as he narrowed his eyes at her, his tone ice cold.

Words failed her as she stared back at him. She didn't know why but all she could do was nod her head slightly while he reprimanded her. Without another word he turned around and quickly climbed the rest of the stairs. It didn't take long for them to climb the rest of the floors and they finally came out onto a small hallway, with a single door at the end. She quickly guessed that this was probably the penthouse apartment in the building, there were no other doors around and as far as she could tell, this was the highest floor in the building.

She couldn't believe her eyes when Damon unlocked the door with his key, revealing the most luxurious apartment she'd ever had the pleasure of stepping foot inside of. It made her apartment look worse than the shady motel they'd been at less than an hour ago, which sucked! She carefully stepped on the mahogany flooring and followed him inside.

The small hallways leading from the front door took them out into the kitchen. The wall to her left had been replaced by windows which gave a spectacular view to Central Park. She topped for a brief second, angling her body out towards the window so she could take in the view. She could spot and old man sitting on a bench for a newspaper, while a man was throwing a baseball to what she assumed was his son. The whole sight was breathtaking and she found herself envious of Damon for being able to wake up to his view every morning, if he wanted to.

The kitchen counter tops were black granite and the whole kitchen gave off a very modern vibe, with very stylish kitchen stools on the edge of the counters. As Elena walked past the kitchen into the loft, she caught eye of bookshelves scattered around the place, filled with books. Figured, of course he read. Damon had always struck her as the type of person who read a lot to obtain information and judging by all of the books in the apartment, she was right. There was also various, foreign paintings that she'd never seen before dotted around the apartment on the walls.

There was also a large 50" television screen which sat in front of a three-piece leather sofa. She couldn't see any other rooms, but she imagined that one of them was probably the bedroom considering that she hadn't spotted a staircase yet. She couldn't stop the bitterness from creeping into her stomach as she took in the whole place. It was her _dream_ apartment. Everything about the place just happened to scream her and she couldn't help but feel a little dissapointed that Damon of all people in the world owned a place like this.

"Of course this is your apartment." Elena snorted, not bothering to hide the fact that she was _slightly_ jealous.

"What's that supposed to mean?" He asked disinterestedly as he knelt down by a bookcase, looking through the set of books he had. It looked as if he was looking for a specific book which she felt was kind of strange considering he'd been home for less than five minutes._  
_

She quickly pushed down her self-conscious from going full cop-mode on him and continued, "Oh come on don't act like you're stupid, your living area is bigger than my entire place! It's ridiculous..."

He turned his head to her, waggling his eyebrows playfully, "Are you second guessing your career path, Gilbert?" He asked, accompanied with a cocky smile. They were in full demand today she noticed, "Finally figured out that you weren't on the better team." He goaded.

"No because I was on the _winning_ team." She replied, unable to resist the urge to rib him about the fact that she caught him against all odds.

"I don't know, I think you're jealous." He smirked and she knew what he was trying to do. He was trying to get a rise out of her, wanted her to bite.

"How were you even able to afford this place?" She accidentally blurted out. It was rhetorical really, she _knew_ how he was able to afford the place. It was meant to be a silent thought to herself, but of course she let it slip out from her dry lips.

"It was with my own money, not that you'd believe me anyway." He replied defensively. "I bought it before I got into-you know."

And for some strange reason she believed him. She didn't know why but he had no reason to lie to her really. They both knew that as soon as she could, she'd find out everything there was to know about the apartment building they were in and would easily find out whether he was lying to her or not. Plus, there was also a sort of warmth in his voice, a sense of genuineness as he spoke. A type that she hadn't noticed in his voice before now. And for that reason alone, she felt the strong urge within herself to believe him.

Her father had always taught her to look for the best in people and Elena tried to live by those words everyday. Some might think it strange that she believed in such things considering she put criminals behind bars everyday and usually dealt with people who had no sense right or wrong, or simply chose to ignore it. But she had to believe that there was at least one part of Damon that was genuine, that was redeemable. Other wise this whole deal that they'd made was pointless. While she'd initially made the deal out of desperation to catch a criminal, she finally noticed that she had the chance to change a man's fate and help guide him from going back to prison, and she had no choice but to try. Even if it had the potential to blow up in her face massively.

"Let's just call it a day and pick it back up tomorrow." Elena sighed. This whole morning with Damon had been emotionally draining. She didn't know how she was going to endure long hours, side by side with him.

"Are you sure? It's only one." He replied, looking at the clock on the wall.

"Yeah it's fine. We wouldn't have been able to do much anyway, I have a lot of paper work to do." She lief effortlessly. She didn't really have any paper work to do. She just wan't physically ready to spend the next seven hours in the company of Damon. He was... intense to say the very least. "Be up at eight tomorrow morning though, we have a lot of work to do."

"Alright Captain." He saluted mockingly.

"And Damon... don't think about running. You know you won't get very far with the anklet." She said from the doorway before she walked out of his apartment leaving him alone with his thoughts.

* * *

_**AN:** I hope you enjoyed the chapter, I really had a lot of fun writing this one. There was also a little bit of Damon's perspective in this chapter that I hope you all enjoyed ;)_

_I'm so sorry that you've all had to wait so long for this to be updated. The truth is that this chapter should have been posted at **least** a week ago but I've recently been having trouble with my laptop and I went without it for over a week. Which sucks, big time. I thought it was the charger at first but it turns out that it's most likely the charger socket in the laptop itself which means sooner or later it's gonna blow or something. So yeah, it looks like a new laptop is on the horizon for me :(. But yeah I just wanted to let you all know just in case, so that if I do fall off the face of the planet for a while, it's not because I've abandoned you all but because my laptop is big pile of junk!_

_Anyway, hopefully in the next chapter things are really going to start moving at a quicker pace. Some things are going to be revealed and we'll get to see our favorite couple in action working together. _


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